It should be very easy. Inserting a tampon shouldn’t hurt. The main things you need to do are get in the right position and RELAX. The muscles of the pelvic floor are very strong, so if you’re not relaxed, it will be very hard to put the tampon in. Get to know your body. Get a mirror and have a look where the tampon is going to go before you start. An easy and convenient position is with one foot on the toilet seat. Wash your hands well then use your index finger to gently push the tampon past your labia (outside folds of the vagina) into your vagina. Push it is as far as it will go- don’t worry, you can’t go too far. Make sure that the strings are hanging out for easy retrieval. When you are done, you shouldn’t be able to feel the tampon. If you do, then you haven’t pushed it in far enough, remove it and start again with a new one. Don’t forget, your pack of tampons will also have usage instructions inside, so have a read of those too. Be sure to change your tampon when it’s full (usually every 3-4 hours depending on your flow) or after 8 hours.. It's very unlikely that there's something wrong with you, particularly if you can get other things in their (for example your finger). But if you're worried, see your doctor.